Dimethylformamide → HCID 86630158, compound

HRID 2425947Notes

Reaction equation

HRID 2425947 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[S:10][CH:11]=[C:12]([C:15]([CH3:17])=O)[C:13]=2[OH:14])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH:18]([N:21]1[CH2:26][CH2:25][N:24]([C:27]([C:29]2[S:33][C:32]([C:34]([NH:36][NH2:37])=[O:35])=[CH:31][CH:30]=2)=[O:28])[CH2:23][CH2:22]1)([CH3:20])[CH3:19].Cl.O1CCOCC1.CN(C)C=O>C(O)(C)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[S:10][CH:11]=[C:12]([C:15](=[N:37][NH:36][C:34]([C:32]3[S:33][C:29]([C:27]([N:24]4[CH2:23][CH2:22][N:21]([CH:18]([CH3:20])[CH3:19])[CH2:26][CH2:25]4)=[O:28])=[CH:30][CH:31]=3)=[O:35])[CH3:17])[C:13]=2[OH:14])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 204431481,4-Dioxane hydrochlorideHCID 442072882-(3,4-Dichlorophenyl)-3-hydroxy-4-(methylcarbonyl)thiopheneHCID 57688151HCID 57688151, compound

Product 1

HCID 86630158HCID 86630158, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

28 mg of 2-(3,4-dichlorophenyl)-3-hydroxy-4-methylcarbonylthiophene (synthesized in accordance with WO2004/108683) and 29.7 mg of 5-(4-isopropylpiperazine-1-carbonyl)thiophene-2-carbohydrazide prepared in Reference Synthetic Example 1 in 2 mL of isopropyl alcohol were heated with 3 mg of p-tosylic acid monohydrate and 25 μL (1 eq) of 4 M hydrogen chloride/dioxane at 105° C. for 8 hours. The reaction solution was further heated with 2 mL of dimethylformamide at 105° C. for 5 hours and cooled to room temperature. The precipitated solid was recovered by filtration and washed with 1 mL of isopropyl alcohol and 1 mL of chloroform, and the resulting crystals were dried to give the desired product (yield 54%).

Workup

  1. filtrationThe precipitated solid was recovered by filtration
  2. washwashed with 1 mL of isopropyl alcohol and 1 mL of chloroform
  3. customthe resulting crystals were dried

Sources & evidence

ORD record
ord-356cc9f6f7e040d6b7cf816776c7c9c9
Source dataset
uspto-grants-2011_06
Patent number
US07968542B2

Reaction notes

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